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Molecules 2015, 20(9), 15631-15642; doi:10.3390/molecules200915631

Ascorbic Acid-Initiated Tandem Radical Cyclization of N-Arylacrylamides to Give 3,3-Disubstituted Oxindoles

1
Hunan Co-Innovation Center for Utilization of Botanicals Functional Ingredients, Hunan Agricultural University, Changsha 410128, China
2
Pre-State Key Laboratory for Germplasm Innovation and Utilization of Crop, Hunan Agricultural University, Changsha 410128, China
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 20 July 2015 / Revised: 18 August 2015 / Accepted: 21 August 2015 / Published: 27 August 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [858 KB, uploaded 27 August 2015]   |  

Abstract

An ascorbic acid-promoted and metal-free tandem room temperature cyclization of N-arylacrylamides with 4-nitrobenzenediazonium generated in situ was developed. This reaction proceeds smoothly through a radical mechanism and provides an environmentally friendly alternative approach to biologically active 3-alkyl-3-benzyloxindoles, avoiding the use of excess oxidants and light irradiation. View Full-Text
Keywords: N-arylacrylamides; 3,3-disubstituted oxindoles; tandem cyclization; ascorbic acid; 4-nitroaniline N-arylacrylamides; 3,3-disubstituted oxindoles; tandem cyclization; ascorbic acid; 4-nitroaniline
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Liu, S.; Cheng, P.; Liu, W.; Zeng, J.-G. Ascorbic Acid-Initiated Tandem Radical Cyclization of N-Arylacrylamides to Give 3,3-Disubstituted Oxindoles. Molecules 2015, 20, 15631-15642.

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